SML2338

4-Octyl itaconate

≥98% (HPLC)

• Sinónimos: β-Monooctyl itaconate, 3-[(Octan-4-yloxy)carbonyl]but-3-enoate, 4-Octyl methylenesuccinate, n-Octyl 3-carboxy-3-butenoate
• Fórmula empírica (notación de Hill): C₁₃H₂₂O₄
• Número de CAS: 3133-16-2
• Peso molecular: 242.31
• Código UNSPSC: 51111800
• NACRES: NA.77

Propiedades

• Análisis: ≥98% (HPLC)
• formulario: powder
• condiciones de almacenamiento: protect from light
• color: white to beige
• solubilidad: DMSO: 2 mg/mL, clear
• temp. de almacenamiento: −20°C
• cadena SMILES: OC(C(CC(OCCCCCCCC)=O)=C)=O
• InChI: 1S/C13H22O4/c1-4-6-8-11(7-5-2)17-13(16)10(3)9-12(14)15/h11H,3-9H2,1-2H3,(H,14,15)/p-1
• Clave InChI: GIRJEIMINMHXQS-UHFFFAOYSA-M

Descripción

Aplicación

4-Octyl itaconate has been used:

• to study its anti-inflammatory effects in macrophages
• to treat bone-marrow-derived macrophages (BMDMs) for BMDM stimulation with nuclear factor-erythroid factor 2-related factor 2 (NRF2)-activating carboxylic acid compounds
• to study its effects on collagen1 expression in systemic Sclerosis (SSc) dermal fibroblasts

Acciones bioquímicas o fisiológicas

4-Octyl itaconate (4-OI) possesses anti-inflammatory effects. It can obstruct glyceraldehyde 3-phosphate dehydrogenase (GAPDH) and glycolysis in macrophages. It can be a good substitute to itaconate due to its thiol reactivity. The electrophilic α and β-unsaturated moieties of 4-OI might help to alkylate the thiol in cysteine residues of proteins through Michael reaction.

The endogenous metabolite itaconate has recently emerged as a regulator of macrophage function. 4-Octyl itaconate is a cell-permeable itaconate derivative that decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo. Esterases in mouse myoblast cells and macrophages hydrolyze it to itaconate, which alkylates cysteine residues on KEAP1, allowing the transcription factor Nrf2 to increase the expression of anti-oxidant and anti-inflammatory downstream genes.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable